Refine Search
Sort by
29313 Glencoe Rd, Kennedyville
$1,100,000
3 Beds ⋅ 2 Baths
Welcome to 29313 Glencoe Rd Kennedyville. Experience waterfront living at its finest with this well-maintained 3-bedroom, 2-bath ranch home. Designed for comfort and relaxation, the home features just a few of the amenities of a bright sunroom, and a spacious walk-out basement. Outside, you'll find two detached garages with additional storage above, offering ample room for vehicles, hobbies, and equipment. An original out building, called the fish house offers a unique perspective of the area. A newer pier with a boat lift and floating dock provides easy access to the water, making it perfect for boating, fishing, or simply enjoying life on the Sassafras River & other tributaries. The property boasts approximately 200 feet of bulkheaded shoreline and a small sandy beach, creating the quintessential waterfront retreat. Elevated views stretch down the Sassafras River and across Freeman Creek, where you can watch abundant wildlife throughout the seasons. Begin each day with breathtaking sunrises over the Sassafras River. This exceptional waterfront property offers the perfect blend of comfort, convenience, and scenic beauty.

29313 Glencoe Rd, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Gunther-McClary Real Estate.

11976 Flour Mill St, Kennedyville
$315,000
3 Beds ⋅ 2 Baths
Welcome to 11976 Flour Mill Street in the charming Village at Kennedyville! Nestled in the heart of this small-town community, this well-maintained 3-bedroom, 2-bath rancher offers comfortable one-level living with an inviting open floor plan perfect for everyday living and entertaining alike. Enjoy relaxing mornings on the welcoming front porch or unwind on the spacious back deck overlooking the backyard. Conveniently located just a short drive to Route 301 for easy northbound or southbound travel, while also being close to the historic waterfront town of Chestertown with its local shops, restaurants, and community events. If you are looking for small-town charm with convenience, this home is a must-see!

11976 Flour Mill St, Kennedyville

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: Unrepresented.

13983 Turners Point Rd, Kennedyville
$567,000
2 Beds ⋅ 3 Baths
Impeccably kept Kentmore Park home with a white picket fence. Over two acres with private rear yard for relaxation. Adorable brick outbuilding for storage, home office, man cave or she shed. Gazebo for al fresco dining, afternoon card games or just enjoying nature. Two additional sheds for storing just about anything. Habitat for many bird species in season. Owl, Heron and Eagle territory year round. This home mixes the old with the new. Character throughout this custom built home. Architectural details, crown and dentil molding. Large kitchen for casual dining and entertaining. Designer countertops and stainless appliances topped off with a Viking range and an antique coal range by AGA. Plenty of gathering space at the elongated island. Large windows bring the outside in to the kitchen. Owner suite is on the main floor. Second floor boasts a super large room and full bath for a guest/ family quarters. There is a beautiful livingroom with a fireplace and a family room with a fireplace and built in bookshelves. Excellent living spaces. The gracious dining room can host many a fine dining experience. The full size basement with indoor and outdoor access offers many possible uses from storage to crafts to games. A lovely sunny screen porch stretches across the back of the house with access to the kitchen and to the owners suite. A step from the porch takes you to the spa/ hot tub in it's own private setting. This home is being offered with an additional lot included. The lot affords this home access to the Kentmore Park Amenities. Beach, Piers, Boat ramp, and the Kentmore Park social association. This listing includes MLS listing # MDKE2005752, 0.11 acre lot on Anglewood Rd, Kentmore Park.

13983 Turners Point Rd, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Unrepresented.

11955 Augustine Herman Hwy, Kennedyville
$330,000
Welcome to this spacious 2,236 square foot, 4-bedroom, 3-bath property located in the heart of Kennedyville, currently configured as a two-unit, multi-use home offering exceptional flexibility. The property can easily be converted back to a single-family 4-bedroom, 3-full-bath residence or utilized as a live/work opportunity with potential storefront space in the front unit while generating rental income from the rear apartment. The rear unit features 2 bedrooms, 2 full bathrooms including a newly added second-floor bath, a full kitchen, laundry, mudroom, and private rear entrance, while the front unit offers 2 bedrooms, 1 full bathroom, a full kitchen, laundry, and a third-floor attic that can easily be converted into additional living space with insulation and electric already roughed in. The owner has completed meticulous structural and mechanical renovations throughout the property, including new plumbing, electrical, HVAC system, roof, insulation, fresh paint, and a newly constructed large full bathroom, ensuring a move-in-ready experience. A fenced rear lot provides parking for up to six vehicles, and the home is certified lead-free. Conveniently located just 10 minutes from Chestertown and 25 minutes from Middletown, the property is also within walking distance to the Kennedyville Firehouse and popular community events such as monthly food truck nights, craft vendor shows, bake sales, and local yard sales.

11955 Augustine Herman Hwy, Kennedyville

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: RE/MAX Chesapeake.

11955 Augustine Herman Hwy, Kennedyville
$330,000
4 Beds ⋅ 3 Baths
This 2,236 sq ft, 4-bedroom, 3-bath property is a versatile live/work or investment opportunity. Currently configured as a two-unit home, it can easily convert back to a single-family residence or generate rental income from the rear apartment while utilizing the front unit as residential or potential storefront space. Each unit is fully self-contained with its own laundry area (washer/dryer) and full kitchen (refrigerator and stove/cooktop), making them highly desirable for tenants. The rear unit features 2 bedrooms and 2 baths, including a newly added second-floor bath, while the front unit offers 2 bedrooms, 1 bath, and a third-floor attic with insulation and electric roughed in for additional living space. Meticulous renovations include new plumbing, electrical, HVAC, roof, insulation, fresh paint, and a newly constructed full bathroom, ensuring a move-in-ready property. A fenced rear lot provides parking for up to six vehicles, and the home is certified lead-free. Located just 10 minutes from Chestertown and 25 minutes from Middletown, the property is near the Kennedyville Firehouse and local events like food truck nights, craft shows, and yard sales. Strong rental potential combined with turnkey upgrades makes this a smart investment for live/work or multi-family income!

11955 Augustine Herman Hwy, Kennedyville

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: RE/MAX Chesapeake.

12089 Blacks Station Rd, Kennedyville
$415,000
4 Beds ⋅ 2 Baths
Charming Cape Cod nestled on a beautiful 2-acre lot offering the perfect blend of space, privacy, and timeless charm! This well-maintained home features a long driveway, 2-car garage, and lovely landscaping that creates wonderful curb appeal. Inside, you’ll find hardwood floors on the main level along with fresh neutral paint throughout the home. The spacious sunroom addition is filled with natural light and offers peaceful views of the picturesque backyard. Nature lovers and gardeners will appreciate the mature fruit trees including apple, pear, and cherry, along with thriving raspberry, blueberry, and blackberry bushes. The flexible main-level bedroom with full bath is ideal for guests, a home office, or convenient one-level living. Upstairs offers generously sized bedrooms with plenty of space and character. Major updates have already been taken care of with a recently updated roof, HVAC system, water softener, and hot water heater. A rare opportunity to enjoy peaceful outdoor living with room to grow! 10 miles to 301, 20 minutes to Chestertown and Middletown.

12089 Blacks Station Rd, Kennedyville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Doug Ashley Realtors, LLC.

How much is your home worth?

Get instant property value now!